WO1984003707A1 - Composition et procede de preadherence de fils de polyester - Google Patents

Composition et procede de preadherence de fils de polyester Download PDF

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Publication number
WO1984003707A1
WO1984003707A1 PCT/CH1984/000042 CH8400042W WO8403707A1 WO 1984003707 A1 WO1984003707 A1 WO 1984003707A1 CH 8400042 W CH8400042 W CH 8400042W WO 8403707 A1 WO8403707 A1 WO 8403707A1
Authority
WO
WIPO (PCT)
Prior art keywords
thread
composition
polyepoxide
alcohol
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CH1984/000042
Other languages
German (de)
English (en)
Inventor
Remy Humbrecht
Peter Beutler
Armin Mueller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Viscosuisse SA
Original Assignee
Viscosuisse SA
Societe de la Viscose Suisse SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=4214555&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1984003707(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Viscosuisse SA, Societe de la Viscose Suisse SA filed Critical Viscosuisse SA
Priority to BR8406457A priority Critical patent/BR8406457A/pt
Priority to DE8484900966T priority patent/DE3476213D1/de
Priority to EP84900966A priority patent/EP0139667B2/fr
Publication of WO1984003707A1 publication Critical patent/WO1984003707A1/fr
Anticipated expiration legal-status Critical
Priority to US08/213,140 priority patent/US5403661A/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/55—Epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2321/00—Characterised by the use of unspecified rubbers

Definitions

  • the invention relates to a composition of a polyepoxide and an amine for pre-adhering polyester threads with good adhesive properties with rubber.
  • the invention further relates to a method for pre-hardening such polyester threads.
  • Threads used to reinforce hoops, hoses, V-belts and conveyor belts are polyester threads.
  • the disadvantage of using polyester threads is that they have insufficiently reactive end groups, with the result that the thread / RFL adhesion is poor. It is therefore necessary to pretreat the polyester thread. This pretreatment, also called pre-adherence, is very often used in fiber production.
  • US Pat. Nos. 3,383,242 and 3,297,468 relate to a process for the pretreatment of polyethylene terephthalate threads by applying a dispersion of a curable combination of a diepoxide and a diamine with primary or secondary functions to said thread (A) (Hardening agent) and (B) a water-dispersible thread preparation.
  • A (Hardening agent)
  • B a water-dispersible thread preparation.
  • This application is carried out on an undrawn thread, which is wound up and later stretched in a second operation using the classic method.
  • the disadvantage of this method is that a composition has to be used which solidifies to a gel-like mass at room temperature after a few hours. The durability of the solution is therefore poor.
  • the thread can not be heated rolls, but 'only in ovens, i.e. even at slow take-off speeds; be stretched. Excess pre-hardening solution would harden on the rollers and a crust would build up in a short time.
  • the threads treated by this method also show deteriorated mechanical properties.
  • polyamide cord i.e. threads already twisted, impregnated with a combination of a polyepoxide and tertiary amine and thermally cured.
  • U.S. Patent 3 79.3 425 and DE-OS 20 56 707 relate to an integrated spin-draw process to prepare polyester filaments, by clicking on the freshly spun and also still undrawn polyester yarn a cooperation ⁇ settlement, containing an alkaline buffered polyepoxy resin, and then hot-stretched and wound the thread treated in this way.
  • the present invention relates to a composition for pre-adhering polyester threads, comprising a polyepoxide and a tertiary amine, and a method for pre-adhering polyester threads by applying the composition according to the invention to the drawn thread.
  • the invention relates to a composition of a
  • R and R 2 are identical or different, is an alkyl having C ⁇ _g, hydroxyalkyl with C ⁇ -g, alkylaryl or aryl, and X is H, OH, NH 2, NHR 3, NR4R5 or Rg, wherein R3, R4,. R5 and Rg are each alkyl with C ⁇ _ or aryl groups.
  • Compound (I) is an amine with at least one tertiary function.
  • the tertiary amine is believed to catalyze the reaction between polyepoxide and polymer works.
  • the group X can also be a primary, secondary or tertiary amine.
  • the second amine function increases the catalytic activity. Thanks to the compound (I), an adhesive layer is formed which, alone or together with an RFL treatment, imparts good adhesion to the thread vulcanized into rubber.
  • the compound (I) is preferably the N, N-dimethylbenzylamine, 3-diethylamino-1-propylamine, 3-dimethylamirio-1-propylamine, tribenzylamine, triethanolamine or triethylamine.
  • the type of polyepoxide of the composition according to the invention is not critical.
  • the glycidyl ethers which are generally prepared by the reaction of epichlorohydrin with an alcohol or a phenol are particularly preferred.
  • the polyepoxide can be saturated, unsaturated, aliphatic, cycloaliphatic, aromatic, heterocyclic or substituted.
  • the connections are either monomers or polymers with at least two epoxy groups per molecule.
  • Examples of such compounds are the epoxy derivatives of bisphenol A or phthalic acid, the epoxyphenol novolac or the epoxy cresol novolac, the glycidyl isocyanurates, the epoxide-containing derivatives of hydantoin, such as the hydantoin triglycidyl ether, the aliphatic Glydidyl ethers such as butanediol diglycidyl ether, ethylene glycol diglycidyl ether or glycerol triglycidyl ether, or even the glycidyl derivatives of triazine such as tris (epoxy-propoxy-2,3) 3-propionyl-l, 3,5-hexahydro-s-triazine ( TEPS).
  • TEPS 3,5-hexahydro-s-triazine
  • TEPS has already been used in the composition according to US Pat. No. 4,121,901 because of its good solubility in water.
  • the composition according to the invention is dissolved in water, alcohol, water-alcohol mixture or in a thread preparation.
  • Thread preparation mainly means products which improve the sliding, antistatic and wetting properties of the synthetic thread.
  • Aids are products which can further improve the adhesion of the thread with rubber, e.g. Carrier or swelling agents such as ethylene glycol, caprolactam, polyvinyl or benzyl alcohol, or solvents which allow the epoxide to diffuse better into the polymer.
  • Carrier or swelling agents such as ethylene glycol, caprolactam, polyvinyl or benzyl alcohol, or solvents which allow the epoxide to diffuse better into the polymer.
  • Wetting agents or surface-active agents such as the commercial products QZ 13 from CIBA-GEIGY and TW 1196 from ZSCHIMMER & SCHWARZ, which are solutions with silicones or ethoxylated compounds, can also be used.
  • Secondary pre-adhering agents can be used.
  • the thread pre-adhered according to the invention can also be subjected to the classic pretreatment agent consisting of a polyepoxide and a blocked polyisocyanate before the RFL treatment.
  • Composition is 5 to 99 and that of compound (I) 0.01 to 6.0, preferably 0.05 to 3% by weight.
  • the rest consists of water, alcohol, water-alcohol mixture or a thread preparation.
  • the invention further relates to a process for the pre-hardening of polyester threads, characterized in that the above-mentioned composition of polyepoxide and tertiary amine is applied to the stretched thread.
  • this method in contrast to the method according to US Pat. No. 3,793,425 and DE-OS 20 56 707, the stretching rollers are not encrusted and the threads have good mechanical properties.
  • polyepoxide and compound (I) is the same as in the composition according to the invention, as is the type of solution.
  • the amount of polyepoxide applied to the thread, and especially compound (I), is quite critical according to the invention.
  • the polyepoxide under 0.05% problems of insufficient adhesion and
  • REPLACEMENT LEAF O ⁇ FI irregular distribution of the polyepoxide along the thread, and an amount of more than 0.5% does not bring better adhesion.
  • maximum adhesion of the thread with rubber is obtained if it is applied in an amount of 2 to 300 ppm, preferably 5 to 100 ppm. All above
  • polyester is understood to mean linear, polycondensed esters, prepared by the reaction of one or more diols of the H0 (CH) n 0H series with 1 - n - 10 with a dicarboxylic acid, preferably terephthalic acid, or a corresponding diester such as dimethyl terephthalate .
  • the polyesters can also be modified with organic or inorganic additives.
  • the polyester used to reinforce elastomers is oriented and stretched to obtain reinforcement filaments with satisfactory mechanical properties for their use.
  • the preferred polyester is polyethylene terephthalate without any restriction regarding the content of carboxyl end groups or of diethylene glycol.
  • the drawn thread is produced using an integrated spin-drawing process.
  • the thread is wound up at take-off speeds of 2000 to 6000 m / min.
  • the composition according to the invention is applied between the last duo and the winder or subsequently during the rewinding process of the drawn thread with one or two dosing pins.
  • Further treatments of the drawn thread may also be considered necessary to improve the sliding or fatigue thereof, e.g. the application of polysiloxanes, silanes, polyethylene glycols, ester or mineral oils.
  • the method according to the invention makes it possible to produce a polyester thread with very good mechanical properties and better adhesion with rubber. On the other hand, this process is simple and very economical, since the stretching process is not negatively influenced.
  • the titer of the polyester thread thus produced is not critical. It is preferably between 500 and 2500 dtex and the number of fibrils between 80 and 500. This thread is particularly suitable for reinforcing the rubber
  • the thread obtained in this way is then ready to be treated in a conventional manner with an RFL bath before vulcanization with rubber. For certain applications, it is vulcanized without RFL impregnation.
  • the thread pre-adhered according to the invention can also be subjected to a second treatment in a classic bath of polyepoxide, mixed with an aqueous dispersion of a blocked polyisocyanate, before it is impregnated and / or vulcanized with the RFL.
  • the invention also relates to the polyester threads thus produced, without restriction with regard to the content of carboxyl end groups.
  • the composition can also be applied to the undrawn thread separately or together with the spin preparation in the separate spinning and stretching process or in the spin-stretching process.
  • the polyepoxide which is advantageously water-soluble, is dissolved in a concentration of 5 to 99% in the amount of water, water-ethanol mixture or solvents such as polyglycols, benzyl alcohol, ester oils. Subsequently, the compound (I) is added in a concentration of 0.01 to 6.0, preferably 0.05 to 3.0% by weight before use of the composition.
  • a polyester thread with a titer of 1100 dtex, consisting of 192 individual fibrils with a high modulus and high strength, is produced by a spin-stretching process as follows:
  • the highly viscous polymer is melted in the extruder at a temperature of 280 to 330 ° C. and extruded through a spinneret. After cooling in a blow chute, the thread is drawn off at normal speed and passed over a preparation roll, where a spinning preparation is applied, and over several pairs of rolls, which are operated at different temperatures and speeds, where it is stretched and fixed.
  • the rollers may, depending on the desired mechanical yarn properties temperatures' 70-245 ° C aufwei ⁇ sen.
  • the roll speeds are such that the spun thread can be stretched up to six times the length. It is wound directly at a take-off speed of 3000 m / min.
  • REPLACEMENT LEAF then impregnated with the R-FL solution, consisting of 20% of a resorcinol-formaldehyde resin and a latex, on a treatment machine and then at 150 ° C for 30 s, then at 235 ° C for 1 min in the classic manner thermally treated. This impregnated cord is then vulcanized into the rubber.
  • R-FL solution consisting of 20% of a resorcinol-formaldehyde resin and a latex
  • the adhesive properties of the vulcanized cord are tested according to the UNIROYAL strip test A-300. This test measures the force required to separate two rubber layers from a vulcanized cord * fabric. A force (pull) of less than 10 daN means poor adhesion, and a force greater than 15 or 20 daN means good to very good adhesion with rubber.
  • the appearance rating indicates how good the rubber on the
  • Cord layer sticks.
  • the highest grade 5 indicates liability in which the tear occurs in the rubber and the cord is not visible on the crack surface.
  • the worst grade 0 indicates an adhesion, in which the tear occurs at the rubber-cord boundary layer, so that no rubber gets stuck to the cord layer.
  • the grades 0.5 to 4.5 are intermediate states. In the present case, the cord has a pull of 7 daN and an appeal rating of 0.
  • the thread production according to the invention takes place as mentioned above, but with the difference that the thread between the last duo and the bobbin winder via a pre-adherent
  • REPLACEMENT SHEET f OMPI Sationsaggregat consisting of a dosing pen, guided and the composition is applied.
  • the composition consists of a polyepoxide, a tertiary amine and a solvent.
  • concentration of the polyepoxide in our examples is 35% by weight, that of the tertiary amine according to the invention is given in the table.
  • the application on the thread is - according to the examples, 0.2% epoxy resin. The thread thus produced is impregnated with RFL and then vulcanized.
  • Example 1 shows how poor the adhesion is if the compound (I) according to the invention is not used in addition to the polyepoxide.
  • Examples 2 to 4 express the catalytic influence of the tertiary amine according to the invention.
  • Example 3 represents an optimal amine concentration at which the pull value is at a maximum.
  • Example 5 only 0.05% polyepoxide was applied to the thread instead of 0.2. The pull value has decreased, but still remains higher than in Example 1, where the poly epoxy application is four times higher, but no compound (I) was used.
  • Examples 6 to 10 are also the subject of our invention. As you can see, the type of. Polyepoxids (di- or triepoxide with different
  • Example 11 a polymer to which ethylene oxide was added prior to melting in the extruder was used.
  • the thread produced has only 5 mol / t carboxyl end groups.
  • the dungsgemass' thread produced inventions in the composition and method has quite good properties Haft ⁇ .
  • Example 8 where the thread has 20 mol / t carboxyl end groups, the adhesive properties are only marginally poorer.
  • the threads of Examples 2 to 11 obtained according to the invention are notable for good processing properties, e.g. no deposits form during twisting. Although the individual filaments are treated, the fatigue of the tire cord produced is not impaired.
  • TEA triethanolamine propionyl-1,3,5-hexahydro-
  • DMPA 3-dimethylamino-l-s-triazine propylamine

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)

Abstract

Cette composition comporte un polyépoxyde et une amine dans laquelle l'amine est une amine tertiaire de formule (I) où n vaut de 1 à 6, R1 et R2 sont identiques ou différents et représentent un alkyle comportant de 1 à 6 atomes de C, un hydroxyalkyle comportant de 1 à 6 atomes de C, un alkylaryle ou un aryle, et X représente H, OH, NH2, NHR3, NR4R5 ou R6, où R3, R4, R5 et R6 représentent chacun un alkyle contenant de 1 à 6 atomes de C ou un aryle.
PCT/CH1984/000042 1983-03-24 1984-03-15 Composition et procede de preadherence de fils de polyester Ceased WO1984003707A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BR8406457A BR8406457A (pt) 1983-03-24 1984-03-15 Composicao e processo para tornar pre-aderentes fios de poliesteres e fios de poliester pre-aderentes
DE8484900966T DE3476213D1 (en) 1983-03-24 1984-03-15 Method for preadhering polyester yarns
EP84900966A EP0139667B2 (fr) 1983-03-24 1984-03-15 Procede de preadherence de fils de polyester
US08/213,140 US5403661A (en) 1983-03-24 1994-03-15 Preadhered melt spun spin-drawn polyester filaments

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH161483A CH654585A5 (de) 1983-03-24 1983-03-24 Zusammensetzung und verfahren zur praeadhaerisierung von synthetischen faeden.

Publications (1)

Publication Number Publication Date
WO1984003707A1 true WO1984003707A1 (fr) 1984-09-27

Family

ID=4214555

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH1984/000042 Ceased WO1984003707A1 (fr) 1983-03-24 1984-03-15 Composition et procede de preadherence de fils de polyester

Country Status (7)

Country Link
EP (1) EP0139667B2 (fr)
BR (1) BR8406457A (fr)
CA (1) CA1246787A (fr)
CH (1) CH654585A5 (fr)
DE (1) DE3476213D1 (fr)
ES (1) ES8700681A1 (fr)
WO (1) WO1984003707A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH677499A5 (en) * 1988-11-24 1991-05-31 Schweizerische Viscose Polyester tyre cord filaments - are impregnated with adhesive to bond to rubber before hot air treatment and single-stage drawing
EP0541107A1 (fr) * 1991-11-06 1993-05-12 Bridgestone Corporation Apprêt collant durcissable aux U.V. et procédés associés
US5547755A (en) * 1988-11-24 1996-08-20 Rhone-Poulenc Viscosuisse Sa Pre-adherized polyester filament yarn for tire cord
US5693275A (en) * 1988-11-24 1997-12-02 Rhone-Poulenc Viscosuisse Method of making an improved pre-adherized polyester filament yarn
US5698646A (en) * 1993-04-30 1997-12-16 Bridgestone Corporation Process for producing elastomeric compound having reduced hysteresis
EP0519927B1 (fr) * 1991-01-14 1998-04-01 Rhone-Poulenc Filtec Ag Procede de fabrication d'un filament de polyester a pre-adherence et nappe de pneumatique realisee avec ce filament de polyester
WO1998045357A1 (fr) * 1997-04-07 1998-10-15 Rhodia Filtec Ag Procede de pre-adhesivite de filaments polyester

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9484123B2 (en) 2011-09-16 2016-11-01 Prc-Desoto International, Inc. Conductive sealant compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1794304A1 (de) * 1959-07-28 1971-11-11 Ciba Geigy Ag Verfahren zum Antistatischmachen von synthetischen Fasern
US3793425A (en) * 1971-12-27 1974-02-19 R Arrowsmith Coating process for polyester substrates
US3962011A (en) * 1972-12-18 1976-06-08 The General Tire & Rubber Company Composite of polyamine bonded to rubber and method for making the same
US4121901A (en) * 1975-01-27 1978-10-24 Rhone-Poulenc-Textile Size composition for improving the adherence of multifilament polymeric yarns to substrates such as rubber, and methods using same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1794304A1 (de) * 1959-07-28 1971-11-11 Ciba Geigy Ag Verfahren zum Antistatischmachen von synthetischen Fasern
US3793425A (en) * 1971-12-27 1974-02-19 R Arrowsmith Coating process for polyester substrates
US3962011A (en) * 1972-12-18 1976-06-08 The General Tire & Rubber Company Composite of polyamine bonded to rubber and method for making the same
US4121901A (en) * 1975-01-27 1978-10-24 Rhone-Poulenc-Textile Size composition for improving the adherence of multifilament polymeric yarns to substrates such as rubber, and methods using same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Buch "Epoxy Resins Chemistry and Technology" from C.A. MAY and Y. TANAKA, MARCEL DEKKER Inc. New York (US) 1983, see page 287 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH677499A5 (en) * 1988-11-24 1991-05-31 Schweizerische Viscose Polyester tyre cord filaments - are impregnated with adhesive to bond to rubber before hot air treatment and single-stage drawing
US5547755A (en) * 1988-11-24 1996-08-20 Rhone-Poulenc Viscosuisse Sa Pre-adherized polyester filament yarn for tire cord
US5693275A (en) * 1988-11-24 1997-12-02 Rhone-Poulenc Viscosuisse Method of making an improved pre-adherized polyester filament yarn
EP0519927B1 (fr) * 1991-01-14 1998-04-01 Rhone-Poulenc Filtec Ag Procede de fabrication d'un filament de polyester a pre-adherence et nappe de pneumatique realisee avec ce filament de polyester
EP0541107A1 (fr) * 1991-11-06 1993-05-12 Bridgestone Corporation Apprêt collant durcissable aux U.V. et procédés associés
US5698646A (en) * 1993-04-30 1997-12-16 Bridgestone Corporation Process for producing elastomeric compound having reduced hysteresis
WO1998045357A1 (fr) * 1997-04-07 1998-10-15 Rhodia Filtec Ag Procede de pre-adhesivite de filaments polyester

Also Published As

Publication number Publication date
EP0139667A1 (fr) 1985-05-08
EP0139667B2 (fr) 1996-05-15
DE3476213D1 (en) 1989-02-23
ES530532A0 (es) 1986-11-16
BR8406457A (pt) 1985-03-12
EP0139667B1 (fr) 1989-01-18
ES8700681A1 (es) 1986-11-16
CH654585A5 (de) 1986-02-28
CA1246787A (fr) 1988-12-13

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